191212-50-7

Upstream product

• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 191212-52-9 (R)-(-)-4-(4-methoxyphenyl)-4-methylhex-5-en-1-al 
• 790260-90-1 (R)-(+)-2-(methoxycarbonyl)-2-(4-methoxyphenyl)propionic acid 
• 1172576-91-8 diethyl(p-methoxyphenyl)aluminum 
• 1108740-07-3 (S)-N,N-diisopropyl O-[1-(4-methoxyphenyl)]ethyl carbamate 
• 1826-67-1 vinyl magnesium bromide 
• 67845-50-5 8-hydroxy-2,6-dimethyl-nona-2,6-diene 
• 624-15-7 geraniol 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1152662-74-2 triethyl(pent-4-yn-1-yloxy)silane 

Downstream Products

• 147821-59-8 (S)-4-(3,7-dimethylocta-1,6-dien-3-yl)phenol 

Relevant academic research and scientific papers

Synthesis of (S)- and (R)-sporochnol by using the allylic substitution of the secondary allylic picolinate

The allylic substitution of secondary allylic picolinates and copper reagents for the construction of a quaternary carbon was applied to synthesis of sporochnol. The enantiomerically enriched allylic picolinate (R)-5 was synthesized through the asymmetric hydrogen transfer of acetylene ketone 11 and the Pd-catalyzed methylation of the iodoallylic alcohol 16a. The key allylic substitution of the allylic picolinate (R)-5 with 4-MeOC6H4MgBr/Cu(acac)2 (2:1) proceeded with 95% chirality transfer with 98% regioselectivity to afford anti SN2' product 6 in 89% yield, which was converted to the methyl ether of unnatural (R)-sporochnol. Similarly, the methyl ether of (S)-sporochnol (the natural form) was synthesized.

Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: Methodology and applications

Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N-diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing contiguous quaternary and tertiary stereogenic centers, and applications to natural product synthesis are also reported.

Quaternary carbon stereogenic centers through copper-catalyzed enantioselective allylic substitutions with readily accessible aryl- or heteroaryllithium reagents and aluminum chlorides

The case of the notorious aryls is solved: The first efficient catalytic and enantioselective method for allylic substitutions that furnish quaternary carbon stereogenic centers by additions of aryl- or heteroarylmetals is reported (see scheme). Highly site- and enantioselective processes begin with readily available organolithium reagents.

Total synthesis of (-)-sporochnol A, the fish deterrent, from a chiral malonate

From a single chiron, the homochiral benzylic malonic acid ester (R)- (+)-2 available with high enantiomeric excess by enzymatic hydrolysis (PLE acetonic powder), enantiomerically pure (-)-sporochnol A 1 was prepared. This versatile method allows preparation of sporochnol 1, via aldehydes 7 and 15, in good overall yield.

The absolute configuration of (+)-sporochnol A, the fish deterrent from the Caribbean marine alga Sporochnus bolleanus

The absolute configuration of (+)-sporochnol A, the fish deterrent from the Caribbean marine alga Sporochnus bolleanus, has been established as S based on the stereocontrolled synthesis of its (R)-(-)-enantiomer from (S)-epichlorohydrin.